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Bidentate Urea Derivatives of <i>p-tert</i>-Butyldihomooxacalix[4]arene: Neutral Receptors for Anion Complexation

2014-01-07Artigo científico Acesso restrito
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datacite.subject.fosCiências Naturais::Ciências Químicas
datacite.subject.sdg06:Água Potável e Saneamento
datacite.subject.sdg11:Cidades e Comunidades Sustentáveis
datacite.subject.sdg13:Ação Climática
dc.contributor.authorMarcos, Paula M.
dc.contributor.authorTeixeira, Filipa A.
dc.contributor.authorSegurado, Manuel A. P.
dc.contributor.authorAscenso, José R.
dc.contributor.authorBernardino, Raul J.
dc.contributor.authorMichel, Sylvia
dc.contributor.authorHubscher-Bruder, Véronique
dc.date.accessioned2026-06-19T11:28:14Z
dc.date.available2026-06-19T11:28:14Z
dc.date.issued2014-01-07
dc.description.abstractThree new bidentate ureidodihomooxacalix[4]- arene derivatives (phenyl 5a, n-propyl 5b, and tert-butyl 5c) were synthesized in four steps from the parent compound ptert- butyldihomooxacalix[4]arene and obtained in the cone conformation, as shown by NMR studies. The binding ability of these neutral receptors toward spherical, linear, trigonal planar, and tetrahedrical anions was assessed by 1H NMR and UV-vis titrations. The structures and complexation energies of some complexes were also studied by DFT methods. The data showed that the association constants are strongly dependent on the nature of the substituent (aryl/alkyl) at the urea moiety. In general, for all the receptors, the association constants decrease with decrease of anion basicity. Ph-urea 5a is the best anion receptor, showing the strongest complexation for F- (log Kassoc = 3.10 in CDCl3) and also high binding affinity for the carboxylates AcO- and BzO-. Similar results were obtained by UV-vis studies and were also corroborated by DFT calculations.eng
dc.description.sponsorshipWe thank the Fundação para a Ciência e a Tecnologia, Project ref PTDC/QUI/69858/2006.
dc.identifier.citationMarcos PM, Teixeira FA, Segurado MA, Ascenso JR, Bernardino RJ, Michel S, Hubscher-Bruder V. Bidentate urea derivatives of p-tert-butyldihomooxacalix[4]arene: neutral receptors for anion complexation. J Org Chem. 2014 Jan 17;79(2):742-751. doi: https://doi.org/10.1021/jo4026012.
dc.identifier.doi10.1021/jo4026012
dc.identifier.eissn1520-6904
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10400.8/16434
dc.language.isoeng
dc.peerreviewedyes
dc.publisherAmerican Chemical Society
dc.relationSynthesis of new homooxacalixarene based anion receptors
dc.relation.hasversionhttps://pubs.acs.org/doi/10.1021/jo4026012
dc.relation.ispartofThe Journal of Organic Chemistry
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectAlkalinity
dc.subjectBinding energy
dc.subjectCarboxylation
dc.subjectMetabolism
dc.subjectUrea
dc.titleBidentate Urea Derivatives of <i>p-tert</i>-Butyldihomooxacalix[4]arene: Neutral Receptors for Anion Complexationeng
dc.typejournal article
dcterms.referenceshttp://pubs.acs.org
dspace.entity.typePublication
oaire.awardNumberPTDC/QUI/69858/2006
oaire.awardTitleSynthesis of new homooxacalixarene based anion receptors
oaire.awardURIhttp://hdl.handle.net/10400.8/16433
oaire.citation.endPage751
oaire.citation.issue2
oaire.citation.startPage742
oaire.citation.titleThe Journal of Organic Chemistry
oaire.citation.volume79
oaire.fundingStreamConcurso para Projectos de I&D em todos os Domínios Científicos - 2006
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameBernardino
person.givenNameRaul
person.identifier.ciencia-idD01B-E5E2-6040
person.identifier.orcid0000-0002-7775-0614
person.identifier.ridA-2338-2010
relation.isAuthorOfPublication915a2334-757a-4011-968c-94e7d391b7ac
relation.isAuthorOfPublication.latestForDiscovery915a2334-757a-4011-968c-94e7d391b7ac
relation.isProjectOfPublication9d3ac079-5af8-4c32-a75a-fd01ceadcdb2
relation.isProjectOfPublication.latestForDiscovery9d3ac079-5af8-4c32-a75a-fd01ceadcdb2

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Three new bidentate ureidodihomooxacalix[4]- arene derivatives (phenyl 5a, n-propyl 5b, and tert-butyl 5c) were synthesized in four steps from the parent compound ptert- butyldihomooxacalix[4]arene and obtained in the cone conformation, as shown by NMR studies. The binding ability of these neutral receptors toward spherical, linear, trigonal planar, and tetrahedrical anions was assessed by 1H NMR and UV-vis titrations. The structures and complexation energies of some complexes were also studied by DFT methods. The data showed that the association constants are strongly dependent on the nature of the substituent (aryl/alkyl) at the urea moiety. In general, for all the receptors, the association constants decrease with decrease of anion basicity. Ph-urea 5a is the best anion receptor, showing the strongest complexation for F- (log Kassoc = 3.10 in CDCl3) and also high binding affinity for the carboxylates AcO- and BzO-. Similar results were obtained by UV-vis studies and were also corroborated by DFT calculations.
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